You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2009-04-06 16:21:04 UTC
Update Date2017-10-23 19:06:01 UTC
HMDB IDHMDB0012210
Secondary Accession Numbers
  • HMDB12210
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).
Structure
Thumb
Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-dimercapto-Octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
dihydro-alpha-Lipoic acidChEBI
dihydro-Lipoic acidChEBI
Dihydrothioctic acidChEBI
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
Dihydrolipoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-dimercapto-OctanoateGenerator
6,8-DimercaptooctanoateGenerator
dihydro-a-LipoateGenerator
dihydro-a-Lipoic acidGenerator
dihydro-alpha-LipoateGenerator
dihydro-α-lipoateGenerator
dihydro-α-lipoic acidGenerator
dihydro-LipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Dihydrolipoic acid, (+-)-isomerMeSH
Dihydrolipoic acid, sodium saltMeSH
Chemical FormulaC8H16O2S2
Average Molecular Weight208.341
Monoisotopic Molecular Weight208.059171136
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
CAS Registry Number462-20-4
SMILES
OC(=O)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyIZFHEQBZOYJLPK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Thia fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.24ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity55.94 m³·mol⁻¹ChemAxon
Polarizability23.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0007-5920000000-99648df42c67f7327a1dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kij-5900000000-7564ff734a37b263a7acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9520000000-35f52ace937d40f6ba6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0920000000-203769a6e5514dfdacceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-0900000000-e0d6ca4b105aaeae3f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vi-9500000000-30fa7bade921a70952d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0960000000-352daa80c3d73329d4b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1930000000-dee930722526f680e10dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9300000000-c53948709f447f46266cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
3-Phosphoglycerate dehydrogenase deficiencyPw000698Pw000698 greyscalePw000698 simpleNot Available
Ammonia RecyclingPw000009Pw000009 greyscalePw000009 simpleMap00910
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Pw000198Pw000198 greyscalePw000198 simpleNot Available
Dimethylglycine Dehydrogenase DeficiencyPw000197Pw000197 greyscalePw000197 simpleNot Available
Glycine and Serine MetabolismPw000157Pw000157 greyscalePw000157 simpleMap00260
Displaying entries 1 - 5 of 8 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028855
KNApSAcK IDNot Available
Chemspider ID408
KEGG Compound IDC02147
BioCyc ID6-S-ACETYL-DIHYDROLIPOATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound421
PDB IDNot Available
ChEBI ID18047
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prehn JH, Karkoutly C, Nuglisch J, Peruche B, Krieglstein J: Dihydrolipoate reduces neuronal injury after cerebral ischemia. J Cereb Blood Flow Metab. 1992 Jan;12(1):78-87. [PubMed:1345759 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.